Free-radical reactions of halogenated bridged polycyclic compounds. Part III. The free-radical addition of alkanethiols, bromotrichloro-methane, and bromine to hexachloromethylenenorbornene

Abstract

The addition of thiols to hexachloromethylenenorbornene is analogous to comparable additions to hexachloro-norbornadiene, and affords 2,3,4,5,5,6-endo-hexachloronorborn-2-en-1-ylmethyl alkyl sulphides as sole products. In contrast, the free-radical addition of bromotrichloromethane and of bromine yields 2-endo-bromo-1,2-exo-3,4,7,7-hexachloro-5-(2,2,2-trichloroethyl)nortricylene and 2-endo-bromo-1,2-exo-3,4,7,7-hexachloro-5- bromomethylnortricyclene, respectively. The formation of these products is discussed in terms of the various possible intermediate radicals.